Citation: LIU Kang, MA Dingxuan, SHI Zhan. Application of Metal-Organic Frameworks for Separation of Hydrocarbon Mixtures[J]. Chinese Journal of Applied Chemistry, ;2017, 34(9): 1006-1016. doi: 10.11944/j.issn.1000-0518.2017.09.170185 shu

Application of Metal-Organic Frameworks for Separation of Hydrocarbon Mixtures

LIU Kang ^a,b ,
MA Dingxuan ^a,b ,
SHI Zhan ^b,,

a.
College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042, China
b.
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, China

Corresponding author: SHI Zhan, zshi@mail.jlu.edu.cn
Received Date: 27 May 2017
Revised Date: 14 June 2017
Accepted Date: 15 June 2017

Fund Project: the Scientific and Technical Development Project of Qingdao 17-1-1-78-jchthe Foundation of the National Natural Science Foundation of China 21601103the Foundation of the National Natural Science Foundation of China 21371069the National High Technology Research and Development Program(863 program) of China 2013AA031702the Natural Science Foundation of Shandong Province, China ZR2016BP04Supported by the Foundation of the National Natural Science Foundation of China(No.21371069, No.21601103), the National High Technology Research and Development Program(863 program) of China(No.2013AA031702), the Natural Science Foundation of Shandong Province, China(No.ZR2016BP04), the Scientific and Technical Development Project of Qingdao(No.17-1-1-78-jch)

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Metal-organic frameworks(MOFs) are a new class of porous materials formed by the self-assembly of metal ions(or metal clusters) and organic ligands. Currently, the application of metal-organic frameworks in separation of light hydrocarbons including methane, acetylene, ethylene, ethane, propylene and propane has attracted tremendous interests. This article briefly reviews the latest development in this field, and discusses the factors influencing the separation effect and the future study prospect.
- metal-organic frameworks,
- light hydrocarbons,
- separation
1. [1]
  Eldridge R B. Olefin/Paraffin Separation Technology:A Review[J]. Ind Eng Chem Res, 1993,32(10):2208-2212. doi: 10.1021/ie00022a002
2. [2]
  Yaghi O M, Li G M, Li H L. Selective Binding and Removal of Guests in a Microporous Metal-Organic Framework[J]. Nature, 1995,378(6558):703-706. doi: 10.1038/378703a0
3. [3]
  HAN Yitong, LIU Min, LI Keyan. Preparation and Application of High Stability Metal-Organic Framework UIO-66[J]. Chinese J Appl Chem, 2016,33(4):367-378. doi: 10.11944/j.issn.1000-0518.2016.04.150439
4. [4]
  Rowsell J L C, Spencer E C, Eckert J. Gas Adsorption Sites in a Large-Pore Metal-Organic Framework[J]. Science, 2005,309(5739):1350-1354. doi: 10.1126/science.1113247
5. [5]
  Han Y, Zheng H, Liu K. In-Situ Ligand Formation-Driven Preparation of a Heterometallic Metal Organic Framework for Highly Selective Separation of Light Hydrocarbons and Efficient Mercury Adsorption[J]. ACS Appl Mater Interfaces, 2016,8(35):23331-23337. doi: 10.1021/acsami.6b08397
6. [6]
  Liu K, Hu H, Sun J. pH Value-Controlled Assembly of Photoluminescent Zinc Coordination Polymers in the Mixed-Ligand System[J]. J Mol Struct, 2017,1134:174-179. doi: 10.1016/j.molstruc.2016.12.075
7. [7]
  Liu K, Sun Y, Hu H. Hydrothermal Syntheses and Characterization of a New Metal-Organic Framework of Gadolinium(Ⅲ) with 2, 4, 6-Tris(3, 5-dicarboxylphenyl-amino)-1, 3, 5-triazine[J]. Polyhedron, 2017,131:8-12. doi: 10.1016/j.poly.2017.04.009
8. [8]
  GONG Wenpeng, KE Xiaofen, LI Zhipeng. Adsorption of Methylene Blue by Phosphomolybdiumtungstic Acid Decorated Metal Organic Framework MOF-5[J]. Chinese J Appl Chem, 2016,33(9):1047-1055.
9. [9]
  Herm Z R, Bloch E D, Long J R. Hydrocarbon Separations in Metal-Organic Frameworks[J]. Chem Mater, 2014,26(1):323-338. doi: 10.1021/cm402897c
10. [10]
  Banerjee D, Liu J, Thallapally P K. Separation of C₂ Hydrocarbons by Porous Materials:Metal Organic Frameworks as Platform[J]. Comments Inorg Chem, 2015,35(1):18-38. doi: 10.1080/02603594.2014.976704
11. [11]
  Li J R, Sculley J, Zhou H C. Metal-Organic Frameworks for Separations[J]. Chem Rev, 2012,112(2):869-932. doi: 10.1021/cr200190s
12. [12]
  Wu H H, Gong Q H, Olson D H. Commensurate Adsorption of Hydrocarbons and Alcohols in Microporous Metal Organic Frameworks[J]. Chem Rev, 2012,112(2):836-868. doi: 10.1021/cr200216x
13. [13]
  Yang R T. Gas Separation by Adsorption Processes[M]. Butterworths, Boston, 1987.
14. [14]
  Czaja A U, Trukhan N, Muller U. Industrial Applications of Metal-Organic Frameworks[J]. Chem Soc Rev, 2009,38(5):1284-1293. doi: 10.1039/b804680h
15. [15]
  Arakawa H, Aresta M, Armor J N. Catalysis Research of Relevance to Carbon Management:Progress, Challenges, and Opportunities[J]. Chem Rev, 2001,101(4):953-996. doi: 10.1021/cr000018s
16. [16]
  Guo X G, Fang G Z, Li G. Direct, Nonoxidative Conversion of Methane to Ethylene, Aromatics, and Hydrogen[J]. Science, 2014,344(6184):616-619. doi: 10.1126/science.1253150
17. [17]
  Zhou S D, Li J L, Wu X N. Efficient Room-Temperature, Au⁺-Mediated Coupling of a Carbene Ligand with Methane To Generate C₂H _x(x=4, 6)[J]. Angew Chem Int Ed, 2016,55(1):441-444. doi: 10.1002/anie.201509320
18. [18]
  Chen Z X, Xiang S C, Arman H D. A Microporous Metal-Organic Framework with Immobilized -OH Functional Groups within the Pore Surfaces for Selective Gas Sorption[J]. Eur J Inorg Chem, 2010,2010(24):3745-3749. doi: 10.1002/ejic.201000349
19. [19]
  Das M C, Xu H, Wang Z. A Zn₄O-Containing Doubly Interpenetrated Porous Metal-Organic Framework for Photocatalytic Decomposition of Methyl Orange[J]. Chem Commun, 2011,47(42):11715-11717. doi: 10.1039/c1cc12802g
20. [20]
  Das M C, Xu H, Xiang S C. A New Approach to Construct a Doubly Interpenetrated Microporous Metal-Organic Framework of Primitive Cubic Net for Highly Selective Sorption of Small Hydrocarbon Molecules[J]. Chem Eur J, 2011,17(28):7817-7822. doi: 10.1002/chem.201100350
21. [21]
  Zhang Z J, Xiang S C, Hong K L. Triple Framework Interpenetration and Immobilization of Open Metal Sites within a Microporous Mixed Metal-Organic Framework for Highly Selective Gas Adsorption[J]. Inorg Chem, 2012,51(9):4947-4953. doi: 10.1021/ic2021275
22. [22]
  Zhang Z, Xiang S, Chen Y. A Robust Highly Interpenetrated Metal-Organic Framework Constructed from Pentanuclear Clusters for Selective Sorption of Gas Molecules[J]. Inorg Chem, 2010,49(18):8444-8448. doi: 10.1021/ic1010083
23. [23]
  Horike S, Inubushi Y, Hori T. A Solid Solution Approach to 2D Coordination Polymers for CH₄/CO₂ and CH₄/C₂H₆ Gas Separation:Equilibrium and Kinetic Studies[J]. Chem Sci, 2012,3(1):116-120. doi: 10.1039/C1SC00591J
24. [24]
  Bloch E D, Queen W L, Krishna R. Hydrocarbon Separations in a Metal-Organic Framework with Open Iron(Ⅱ) Coordination Sites[J]. Science, 2012,335(6076):1606-1610. doi: 10.1126/science.1217544
25. [25]
  He Y, Krishna R, Chen B. Metal-Organic Frameworks with Potential for Energy-Efficient Adsorptive Separation of Light Hydrocarbons[J]. Energy Environ Sci, 2012,5(10):9107-9120. doi: 10.1039/c2ee22858k
26. [26]
  Hu Y X, Xiang S C, Zhang W W. A New MOF-505 Analog Exhibiting High Acetylene Storage[J]. Chem Commun, 2009(48):7551-7553. doi: 10.1039/b917046d
27. [27]
  Liu K, Li B, Li Y. An N-Rich Metal-Organic Framework with a rht Topology:High CO₂ and C₂ Hydrocarbons Uptake and Selective Capture from CH₄[J]. Chem Commun, 2014,50(39):5031-5033. doi: 10.1039/c4cc00375f
28. [28]
  Liu K, Ma D, Li B. High Storage Capacity and Separation Selectivity for C₂ Hydrocarbons over Methane in the Metal-Organic Framework Cu-TDPAT[J]. J Mater Chem A, 2014,2(38):15823-15828. doi: 10.1039/C4TA03656E
29. [29]
  Xiang S, Zhang Z, Zhao C. Rationally Tuned Micropores within Enantiopure Metal Organic Frameworks for Highly Selective Separation of Acetylene and Ethylene[J]. Nat Commun, 2011,2204. doi: 10.1038/ncomms1206
30. [30]
  Yang S H, Ramirez-Cuesta A J, Newby R. Supramolecular Binding and Separation of Hydrocarbons within a Functionalized Porous Metal-Organic Framework[J]. Nat Chem, 2015,7(2):121-129.
31. [31]
  Cui X L, Chen K J, Xing H B. Pore Chemistry and Size Control in Hybrid Porous Materials for Acetylene Capture from Ethylene[J]. Science, 2016,353(6295):141-144. doi: 10.1126/science.aaf2458
32. [32]
  Bao Z, Alnemrat S, Yu L. Adsorption of Ethane, Ethylene, Propane, and Propylene on a Magnesium-Based Metal-Organic Framework[J]. Langmuir, 2011,27(22):13554-13562. doi: 10.1021/la2030473
33. [33]
  Wang Q M, Shen D M, Bulow M. Metallo-Organic Molecular Sieve for Gas Separation and Purification[J]. Micropor Mesopor Mater, 2002,55(2):217-230. doi: 10.1016/S1387-1811(02)00405-5
34. [34]
  Ploegmakers J, Japip S, Nijmeijer K. Mixed Matrix Membranes Containing MOFs for Ethylene/Ethane Separation-Part B:Effect of Cu₃BTC₂ on Membrane Transport Properties[J]. J Membr Sci, 2013,428:331-340. doi: 10.1016/j.memsci.2012.11.013
35. [35]
  Nicholson T M, Bhatia S K. Electrostatically Mediated Specific Adsorption of Small Molecules in Metallo-Organic Frameworks[J]. J Phys Chem B, 2006,110(49):24834-24836. doi: 10.1021/jp065102b
36. [36]
  Nicholson T M, Bhatia S K. Role of Electrostatic Effects in the Pure Component and Binary Adsorption of Ethylene and Ethane in Cu-Tricarboxylate Metal-Organic Frameworks[J]. Adsorpt Sci Technol, 2007,25(8):607-619. doi: 10.1260/0263-6174.25.8.607
37. [37]
  Wang S, Yang Q, Zhong C. Adsorption and Separation of Binary Mixtures in a Metal-Organic Framework Cu-BTC:A Computational Study[J]. Sep Purif Technol, 2008,60(1):30-35. doi: 10.1016/j.seppur.2007.07.050
38. [38]
  Lamia N, Jorge M, Granato M A. Adsorption of Propane, Propylene and Isobutane on a Metal-Organic Framework:Molecular Simulation and Experiment[J]. Chem Eng Sci, 2009,64(14):3246-3259. doi: 10.1016/j.ces.2009.04.010
39. [39]
  Jorge M, Lamia N, Rodrigues A E. Molecular Simulation of Propane/Propylene Separation on the Metal-Organic Framework CuBTC[J]. Colloids Surf A, 2010,357(1/2/3):27-34.
40. [40]
  Rubes M, Wiersum A D, Llewellyn P L. Adsorption of Propane and Propylene on CuBTC Metal-Organic Framework:Combined Theoretical and Experimental Investigation[J]. J Phys Chem C, 2013,117(21):11159-11167. doi: 10.1021/jp401600v
41. [41]
  Fischer M, Gomes J R B, Froeba M. Modeling Adsorption in Metal Organic Frameworks with Open Metal Sites:Propane/Propylene Separations[J]. Langmuir, 2012,28(22):8537-8549. doi: 10.1021/la301215y
42. [42]
  Yoon J W, Jang I T, Lee K Y. Adsorptive Separation of Propylene and Propane on a Porous Metal-Organic Framework, Copper Trimesate[J]. Bull Korean Chem Soc, 2010,31(1):220-223. doi: 10.5012/bkcs.2010.31.01.220
43. [43]
  Wu X F, Bao Z B, Yuan B. Microwave Synthesis and Characterization of MOF-74(M=Ni, Mg) for Gas Separation[J]. Micropor Mesopor Mater, 2013,180:114-122. doi: 10.1016/j.micromeso.2013.06.023
44. [44]
  Bohme U, Barth B, Paula C. Ethene/Ethane and Propene/Propane Separation via the Olefin and Paraffin Selective Metal Organic Framework Adsorbents CPO-27 and ZIF-8[J]. Langmuir, 2013,29(27):8592-8600. doi: 10.1021/la401471g
45. [45]
  Bae Y S, Lee C Y, Kim K C. High Propene/Propane Selectivity in Isostructural Metal Organic Frameworks with High Densities of Open Metal Sites[J]. Angew Chem Int Ed, 2012,51(8):1857-1860. doi: 10.1002/anie.v51.8
46. [46]
  Geier S J, Mason J A, Bloch E D. Selective Adsorption of Ethylene over Ethane and Propylene over Propane in the Metal-Organic Frameworks M₂(dobdc) (M=Mg, Mn, Fe, Co, Ni, Zn)[J]. Chem Sci, 2013,4(5):2054-2061. doi: 10.1039/c3sc00032j
47. [47]
  Yang R T, Kikkinides E S. New Sorbents for Olefin/Paraffin Separations by Adsorption via π-Complexation[J]. AIChE J, 1995,41(3):509-517. doi: 10.1002/(ISSN)1547-5905
48. [48]
  Jiang W J, Yin Y, Liu X Q. Fabrication of Supported Cuprous Sites at Low Temperatures:An Efficient, Controllable Strategy Using Vapor-Induced Reduction[J]. J Am Chem Soc, 2013,135(22):8137-8140. doi: 10.1021/ja4030269
49. [49]
  Qin J X, Wang Z M, Liu X Q. Low-Temperature Fabrication of Cu(Ⅰ) Sites in Zeolites by Using a Vapor-Induced Reduction Strategy[J]. J Mater Chem A, 2015,3(23):12247-12251. doi: 10.1039/C5TA02569A
50. [50]
  Chang G G, Huang M H, Su Y. Immobilization of Ag(Ⅰ) into a Metal-Organic Framework with -SO₃H Sites for Highly Selective Olefin-Paraffin Separation at Room Temperature[J]. Chem Commun, 2015,51(14):2859-2862. doi: 10.1039/C4CC09679G
51. [51]
  Zhang Y M, Li B Y, Krishna R. Highly Selective Adsorption of Ethylene over Ethane in a MOF Featuring the Combination of Open Metal Site and π-Complexation[J]. Chem Commun, 2015,51(13):2714-2717. doi: 10.1039/C4CC09774B
52. [52]
  Chang G G, Bao Z B, Ren Q L. Fabrication of Cuprous Nanoparticles in MIL-101:An Efficient Adsorbent for the Separation of Olefin-Paraffin Mixtures[J]. RSC Adv, 2014,4(39):20230-20233. doi: 10.1039/C4RA02125H
53. [53]
  Liao P Q, Zhang W X, Zhang J P. Efficient Purification of Ethene by an Ethane-Trapping Metal-Organic Framework[J]. Nat Commun, 2015,68697. doi: 10.1038/ncomms9697
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